


Understanding

by SupernaturalFallenAngel



Category: Supernatural
Genre: Castiel and Jack bonding, Castiel's Past, Dean and Jack bonding, Dean's past, Fix-It, Gen, John Winchester's A+ Parenting, Purgatory fix it, Sam and Jack bonding, Sam being Lucifers vessel, Sam explains his past to Jack, Supportive Castiel, Supportive Dean, The Cage, Unresolved Issues, mention of demon blood, past trauma, voicemail fix-it
Language: English
Status: In-Progress
Published: 2017-12-12
Updated: 2017-12-12
Packaged: 2019-02-08 17:30:10
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,115
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12869523
Author URL: https://archiveofourown.org/users/SupernaturalFallenAngel/pseuds/SupernaturalFallenAngel
Summary: Jack becomes curious about the Winchester's and Cas's past, specifically Sam's since he knows a lot about Lucifer. He's heard them say they've done bad things but what could they have possibly done? Sam decides to tell Jack everything even if they all haven't quite got over it yet, Castiel and Dean help as much as they can. A retelling of Supernatural through different perspectives and commentary, Set loosely after 13x06 (without Jack leaving) but thats kinda irrelevant.





	Understanding

**Author's Note:**

> Hello readers!  
> I kinda wanted to write this because the Winchesters just have such an extensive past that really doesn't get brought up all to often.In s12 I was kinda waiting for them to tell Mary about their lives since I thought she'd be pretty interested but I guess the show didn't really want to rehash all that. Now with Jack I think its the perfect opportunity since he's kinda a mirror for each of them especially Sam ( I may be a little biased towards Sam)

Jack sat in his room in this strange bunker just thinking. He wasn't quite sure who he was meant to be or exactly _what_ he was and with so many people telling him different things he had no idea how he was ever going to work it out. What he did want to do was start by learning a bit more about the world around him, what even was this strange bunker that seemed impervious to supernatural threats? Who exactly was his biological father and why did everyone hate him so much? and how had  the Winchesters and the angel Castiel even gotten so mixed up in this? He had a lot of questions about his mentors lives, how they all new each other so intimately well and could communicate almost wordlessly, and the strange conversations he heard from Sam and Dean, Sam talking about when he was the freak and Dean didn't kill him; what on earth had that meant?

It was a frustrating trail of breadcrumbs he was trying so hard to pick them up, he may as well just ask them straight to their faces. The most recent thing he could think of was when Sam and Dean had been discussing a case where a demon had been pretty much gutted, blood completely drained. Dean had said something about maybe someone going after the demon blood that made Sam pale and look awkwardly away so obviously even he had noticed it. Whatever that was Sam had definitely had past experience with it before. If he was gonna figure this all out he was gonna start with his first lead.

He opened his bedroom door and walked towards the war room where Castiel now sat occupied with a newspaper. It was a peculiar sight and was something that just looked so oddly _human_ to Jack. When Castiel noticed him he looked up and smiled warmly.

'Hello Jack' 

he tried to mirror the warm smile and greeting

'Hello Castiel'

He saw a very brief tug on the edge of Cas's lips and wondered if he had noticed him trying to copy his behaviour.

'Is there something I could help you with?'

'Yes actually... I wanted to know more about more about your lives,' He seated himself in the chair next to Cas.  

'You certainly don't seem like any of the other angels and Sam and Dean don't seem like the other humans I met.'

'That is true, Sam and Dean are definitely..... different and so am I, I think we all changed each other in a way'

'But how did you even meet?'

Castiel struggled to answer for a few seconds, 'Well... that is a very long story'

well if Cas wasn't going to tell him that, he tried for something different 'The other day when Sam and Dean were talking about a case, they said something about demon blood and Sam sorta looked.... different. So did Dean for that matter, why?'

If Castiel was having trouble answering the last question if was nothing compared to this, 'They've had some negative experiences before... A long time ago. But it really isn't my story to tell'

'Who's is it?'

'Well I suppose it's Sam's'

As is summoned by his name Sam now walked in and towards the coffee machine.

'Whats mine?'

Castiel looked very nervous with the entire topic of conversation making Jack evermore curious.

'Jack just had a few questions about us, and our lives.'  

'Alright then' Sam finished off making his coffee and sat opposite Cas and Jack in what was most notably the comfiest chair.

'Fire away.' 

'Well how did you learn all of this?' Jack gestured vaguely to everything around them.

'Hunting, monsters, cases. Most other humans don't seem to know how to do it'

'Well our father taught us how to hunt, what kills what and how to survive basically.'

'Your father?' Jack seemed a little shocked to remember the Winchester must of had a father at some point,

'Where is he now?' For Jack had heard very little discussion about him.

Sam seemed a little sadder at the question and Castiel looked sympathetic making Jack regret asking the question already.

'He's... dead. He died a long time ago though, killed by a demon.' The Winchesters lives were quickly becoming even more of a mystery than Jack had even begun to think of. He decided to try something more current then,

'Your recent case, in Boulder you and Dean were acting strange about the demon being gutted something about demon blood?' Jack instantly notice Sam stiffing and looking..... shameful?

before he answered however Cas spoke,

'Jack it a very long, bloody tale that's really not worth...'

'Cas its alright.' Sam cut in, quickly dismissing Castles deflection, 'Maybe telling him will help him understand our world a bit more, though Jack if you really want to know the full story I should get Dean' While Sam seemingly about to explain everything made Jack ecstatic he still felt just a little uncomfortable around Dean, he wasn't willing to sacrifice his one shot at information though. 

'Okay'   


Sam quickly got up and left the table leaving his untouched luke warm coffee.

Cas still looking slightly uncomfortable glanced at Jack and breathed a sigh heavy with emotion.  
'Jack, there are some things.... Life hasn't always been easy for Sam and Dean and some of their history still brings them a lot of pain, if you truly wish to question them you should do so cautiously. Theres a lot in their past, in my past included, that we're all not proud of and is difficult to explain.'

Jack really had no response to that but was saved from answering when Sam walked in with a reluctant looking Dean in tow. 

'Really Sam? we're gonna do story time with our lives? why exactly do you want us to rehash everything again?'

'Alright look we don't have to say everything, and besides... kids probably will find out other ways like those stupid books.' 

'ughh don't remind me, fine but don't expect me to turn into Ms Lorista'

'Who?'

'That librarian you loved who used to read storybooks out loud.'

'What? never mind.' 

Both Winchesters had only spared quick glances at Jack and Cas during their bickering and now turned their full attention towards them and seating themselves comfortably. 

'So Jack, what do you want to know?' Sam said 

'Well, everything' 

'Ok, lets start at the beginning. When Dean and I were very very young, our mother was killed in a fire set by a demon named Azazel.' Sam hesitated very briefly, 'He also did something to me, but I'll get to that later.'  
Jack was a little confused considering he knew the Winchester's mom had been alive recently but he didn't dare interrupt. 

'From there our dad became obsessed with finding her killer, raising us so that we could protect ourselves. He taught us how to shoot a gun, what kills what and how to cover your tracks from every type of creature....As well as cops.'  
Castiel was also listening intently, admittedly he knew very little about the Winchesters childhoods.

Dean chimed in, 'But he was also a bit of a drill sergeant, we were never allowed to stay anywhere long, meaning we never made any friends or had any type of home. We followed everyone of his orders to the T, too afraid to say anything but 'yes sir.' ' 

Sam was a little shocked at Deans admittance of the downfalls of their childhood, he used to never say a words against John. Cas meanwhile was having a very hard time imagining Dean following someones orders and calling them Sir. 

Sam continued on to Jack, 'Well this went on for majority of our childhoods until I started to hate hunting. I tried to leave, I went to Stanford to become a Lawyer and had a girlfriend called Jessica' 

Castiel again thought how strange it would've been if Sam had stayed there and become a lawyer, he was pretty sure it still wouldn't of lasted long considering the world would of ended. 

'Dean showed up and told me Dad was missing. We went out to look for him but only ran into a spirit, eventually I went back to Stanford but I was too late. My girlfriend Jessica was killed, the same demon who'd killed out mother murdered her.' 

Both Dean and Castiel cast sympathetic looks.

'Why?' Jack couldn't help but wonder out-loud.

'Uhh that's a little complicated but I'll get to it I promise. After her death, I couldn't keep going to stanford. I set out with Dean and we began hunting together again while looking for Dad. At the time I also started having visions; I saw people dying before it happened so Dean and I would try to save them. Most the time we were successful but sometimes not.'

this seemed to really interest Jack, 'You have powers?!' maybe Sam had powers like him and had learned to control them, he even seemed to have used them to save people.

'Well... had them, I'm pretty sure they're gone now.' Jack looked slightly crestfallen but Sam continued on happy to change subject.

'We ran into this one demon often called Meg, who tried to kill us.'

'Alot' added Dean grumpily. 

'We also found Dad who said he was apparently very close to finding the demon who killed our mom. Well we got a little too close and we ended up in this giant car crash, Dean was badly injured and dying.'

'I thought Dad was trying to summon the demon to kill it but turns out he had other plans; he made a deal, his life for Dean's.' 

This Castiel was very well aware of, the angels thought it was John Winchester who would shed blood in hell first and break the first seal. 

'And that's how he died?' 

Dean nodded, 'but right before he did he told me something, that I'd have save Sam or kill him.'

Castiel turned towards Dean sharply, 'He told you that? How much did he already know?'

Dean simply shrugged. 'No clue, would've been nice though if he'd mentioned any other information he had.' 

Sam turned back to the story. 'Well anyway, Dean and I continued hunting with a lot of help from another man called Bobby. A few other things happened, we found out I was immune to this strange demonic virus and we become close friends with these other hunters; Ellen and Jo. We also found other kids who were similar to me, they all had abilities and most had been visited by the demon when they turned 6 months old.' 

'I was taken to an abandoned town and pitted against some of the other kids, Azazel told us that only one would make it out and become his champion. He was looking for the strongest of us to use in his ...plans'

'And you were the survivor?' Jack asked drawing a logical conclusion 

Dean was looking grievous at this part of the story and focused on drawing patterns on the wooden table.

'Not exactly, me and this one other kid became the only two left. I tried to convince him not to fight but he wouldn't listen, I won but I wouldn't kill him. I turned my back on him and........ he uh... stabbed me. Azazel opened a door to hell and I died pretty fast after that'

There was a small gap of silence. Dean decided to continue his part in the story,

'I couldn't deal with Sam being dead so I did something stupid to get him back, I went and sold my should in return for for Sam alive. I was allowed one year before I had to go to hell.'

Dean went back to drawing imaginary shapes on the table and Jack now looked between the two brothers realising a little more just how strong their bond was. Taking as his cue to continue Sam kept going,

'After that we managed to kill Azazel with the colt, a gun that could kill anything. We kept hunting while trying to find a way to break Deans deal and also learned of a new demon, Lilith, who wanted me dead'

this next bit Sam had to prepare himself very quickly for, it was a long time ago but it still stung just a bit. 

'We also met a demon who claimed she could help us, Ruby.'  
Dean unhelpfully piped up, 'I voted that we stab her.'

Sam looked down dejectedly, 'If only.' 

'She gave us this knife' Sam held up the demon-killing knife to illustrate his point. 'And taught us how to make hex bags that hid us from demons.'

'Why was she helping you so much?' 

'At the time she told us it was because she remembered what it was like to be human and she wanted Lilith dead. Truthfully, she was there to manipulate me; she was working for Lilith the whole time. She helped me use my powers more and more until I could exercise demons and save the vessels.'

the story didn't get much easier from and Sam let out a deep sigh before continuing.  
'A year went by and we found out Deans contract was owned by Lilith. We set out to kill her put basically everything got screwed, Dean was taken.....' Sam struggled remembering his own failure to save Dean, 'to hell.'

A silence once again settled over the group before Cas spoke up.

'Before we continue the next part, would anybody else like something to eat or drink?'

Dean couldn't help but let out a small laugh at such an obvious and strange way of breaking the silence but still took him up on the offer, 'Yeah sure, I'll have a beer.'  
Cas threw him a slightly disapproving look but didn't say anything and went to go get it.

Jack looked on the brothers with wide eyes, a little struck with awe. 'So you guys have really done a lot huh?' 

'You don't know the half of it kid.' 

'How did you ever get out if hell Dean?" 

Castiel returned with a beer in hand and a cup of tea for himself, he been trying to acclimatise to human food in beverage so he could enjoy in much the same ways humans did. Often it went with varying success; he decided that no matter how hard he tried he could never like mushrooms. 

'I suppose that's my cue for the story',

'I was one of heavens soldiers, i followed orders, I gave commands and did everything i could to help heaven. I had been tasked with getting one man out of hell, Dean Winchester.' 

'Me and a some others lay siege to hell to reach Dean, a few angels died but I reached Dean and brought him back to earth. I than began trying to communicate and eventually meet him.'

Dean nearly laughed a that, 'Well you came in pretty guns blazing, walking into the barn, shattering all the lights. Show off. Also you really had to let me dig myself outta that grave?'

Castle was a little bit smug about his entrance, he'd known he made quite the scene. Although in retrospect he felt a little bad for leaving Dean in that grave,  
'Dean I do apologise, my orders were to rescue you and feeling my job was completed, I left. I didn't pay much attention to where exactly you were put back together.'

Dean just took a swig of the beer and didn't speak, Castiel took that as an accepted apology. 

'Wait, why did heaven order you to rescue him specifically?' Jack asked

'Well I wasn't one to question orders but I was told he was needed, that he was the 'righteous man', you'll understands heavens true motives later.'

this seemed to satisfy Jack who nodded and waited for the next part.

'Meanwhile while Dean was gone, I had gone a little off the rails.' continued Sam

'I went a little kamikaze, tried to bargain with every crossroads demon for Deans soul back and was halfway to getting myself killed when Ruby jumped in. She convinced me that revenge was better than my pointless death and told me how I could get it. It came at a cost though; I had to do something dark and wrong.'

Everybody except Jack began to look a little more uncomfortable most notably Sam who looked like he wanted to disappear. 

'Turns out the demon who killed our mother had also done something to me, he'd fed me demon blood. Ruby told me that if I drank more of it I'd be stronger, strong enough to kill Lilith.' 

Sam continued to grimace and Jack was now quite shocked and hung on Sam's every word.

'So i did something so twisted, knowing it was wrong and drank her blood. I didn't think my life meant anything without Dean and if all I could was kill the one who'd put him in hell, well, I was going to do everything it took, regardless of what it did to me.'

'Dammit Sam' muttered Dean.

Sam had noticed Deans comment but continued on as if he hadn't.

'When Dean came back, I was well, over the moon. It was the one thing I'd wished for most and now it was here in front of me, I was just not sure about telling Dean everything I'd been doing with Ruby. I told myself I'd just give him time to adjust, or that it really didn't matter now. It was probably one of the worst decisions I've made.'

'I stopped drinking the blood and tried to pick myself up a little. Whatever had saved Dean I was immensely grateful but a little worried and needed to be ready to face whatever was coming. Than Dean told me it was an angel and a lot of my skepticism just drained away, back then I'd actually been kinda religious. I thought since we fought demons and all matter of other monsters that angels and god must exist, I even used to pray pretty much once a day when I was young.' 

'I never knew that.' spoke Cas softly 

'Well I was pretty anxious to meet them despite Deans warnings. There was a demon being raised called Samhain and Castiel and this other angel called Uriel arrived to tell us this was the breaking of one of the 66 seals. Basically the locks on Lucifers cage.'

Jack couldn't help but jump at the name, 'Lucifer? like my father?'

'The one and only' Dean said

'We were told that we needed to prevent the seals from breaking and it was Lilith who was doing the breaking. This was my first meeting with angels and well..'

Castiel finished for him, 'I'm guessing it wasn't exactly what you thought it would be like? Sam when we first met I called you Sam Winchester, the boy with the demon blood and I apologise. I was simply stating one of the few facts I knew about you and I can only imagine how damaging that would have been and I have never said sorry.'

Sam waved him away pretty quickly 'Long time ago Cas, you've long since been forgiven.'

'Anyway Dean and I continued hunting, learned a little more; like that our mother originally made a deal with Azazel to bring back our father in exchange for 'a favour' which had bee the demon blood. We also met Anna, an angel who had fallen to experience humanity and forgot she was an angel we helped her find her grace and she disappeared.'

'Mainly because she was being hunted by us, it is seen as a terrible sin to fall from heaven.' Added Cas a little sadly.

Dean continued, 'After that it was a race to stop the seals breaking, we were doing all we could to stop Lilith and sometimes that meant getting our hands dirty. We captured a demon called Alastair' Dean spoke the name as if it were poison, 'He was in charge of my torture in hell and we needed to know were Lilith was going to hit next, Cas and Uriel asked me to get'em to talk.'

'Asked is putting it lightly. Dean I'm so sorry for making you do that.' Cas said giving an apology for the second time an undoubtedly getting ready to give more.

'Cas that wasn't on you.' Dean held eye contact with Cas to get him to understand he was genuine. 

Jack was curious what Castiel would have been like during the time the Winchesters were explaining. He certainly seems to have changed a lot, they all had.

Sam readied himself for the part that he would have to tell, he thought about how he could phrase so Jack didn't become scared of his own powers and how to say it without bringing up a bunch of memories he'd tried very hard to compartmentalise and push down. 

'This next bit gets a bit dark. Jack I want you to remember that these we my choices and had little to do with my powers being purely evil. You can make your own choices, I do believe that you will. Even if I didn't..' 

'I still wanted revenge on Lilith and thought killing her would mean the end of the apocalypse. The angels said that Dean would be the one to do it but I didn't believe it, I didn't want him to bear that burden, especially just after he'd come out of hell. I was reckless, stupid and vain, I decided to kill her doing whatever it took even it meant I'd have to go behind Dean's back. I went to Ruby, asked her what I had to do and she told me; I had to go back to drinking the blood, and I agreed. I became dependent on her, craving it bad. I couldn't hide it forever and it came out in one of the worst possible ways.'

Sam continued to fidget with everything around him, particular his mug. Dean and Castiel listened sombrely.

'We were trying to help Cas's vessel, Jimmy Novak, and it came to a fight between us and a bunch of demons. I grabbed one and... it was right there. It was too tempting and..... I...I started to drink it.'

'I turned around and Dean and Cas had seen everything, I sat there a monster with blood on his face. I tried to forget about it briefly, thinking about how it had come in useful to exorcise the last demons even if i was turning myself into.. not me.' 

Dean had held his tongue long enough. 'Hang on just a sec, I think that it's also important to explain that hell was also fully manipulating Sam into this. They had a very big hand in what happened.'

Sam spoke quietly, 'Nobody forced me to drink it initially Dean. that one's on me.'

Dean looked like he wanted to argue further but thought he'd hold his protests till the end.

'Well after that Cas left and it was just me and Dean. We got a call from Bobby asking us to help with something and well, when we got there, Bobby and Dean locked me in the panic room to.... detox.'

Jack almost couldn't believe it, how had they ever come back from that? how are they still even on speaking terms?

'What followed was pretty ugly. Hallucinations, so many hallucinations.... Pain... and cravings. I lost sight of who I was, the only thing I could remember was that I had to kill Lilith. Then miraculously the door opened.'

Dean inturrupted 'Yeah I'm still not sure how that even happened, it couldn't of been Ruby. Thing was made or iron and covered in demon traps.' 

Castiel was suddenly struck by guilt as he realised he'd never told the Winchesters it had been him. If he wasn't an angel he would of paled.

'That was me..... I'm so sorry. I know...what..... I understand if you might need to take some time to think about that.' Cas got up and was turning to leave before Sam got over his shock.

'Hold up, Cas. We forgive you, you acted on heavens order. We all had our role to play in the apocalypse and as far as I can tell you're not nearly as to blame as me. It's all in the past anyway, it take a lot more than that for us to kick you out'

Cas couldn't help but smile as he wondered how lucky he was to be apart of the Winchesters family and how ready to forgive they were.


End file.
